Water → 1-(1-Ethylpropyl)-6-iodo-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

HRID 966011Notes

Reaction equation

HRID 966011 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH2:14][CH2:15]Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32]>>[CH2:31]([CH:30]([N:29]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([I:12])[C:6]=3[N:5]=[C:4]([CH3:13])[C:3]=2[CH2:14][CH2:15]1)[CH2:33][CH3:34])[CH3:32]

Participants

5

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 120193-PentanamineHCID 222495054-Chloro-3-(2-chloroethyl)-8-iodo-2-methylquinoline

Product 1

HCID 222499561-(1-Ethylpropyl)-6-iodo-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

Procedure

4-Chloro-3-(2-chloroethyl)-8-iodo-2-methylquinoline (900 mg, 2.46 mmol) was dissolved in 3-aminopentane (10 mL), followed by adding p-toluenesulfonic acid (900 mg). The mixture was sealed at 200° C. for six hours. Water was added to the reaction mixture, extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over magnesium sulfate, and then evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (450 mg, 1.18 mmol) as white crystals.

Workup

  1. customThe mixture was sealed at 200° C. for six hours
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c7264dcc751d4a208965a960a6ce3a17
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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